The opening of a new restaurant in the village of Chestertown, Maryland is a watershed event in Eastern Shore dining. The aptly named Watershed Alley has designed its food, its setting, and its tasteful architecture to highlight the remarkable resources of its local surroundings.
The true origins of the restaurant can be traced to the origins of the Chesapeake Bay itself. For centuries, the Chesapeake Bay watershed has provided a boundless variety of seafood and local farm food for the greater Chesapeake region. Watershed Alley’s distinctive cuisine, atmosphere, and service draw upon and extend this tradition, offering creative options that highlight traditional ingredients and flavors.
Based on 55 reviews, the restaurant has received a rating of 4.5 stars. Price
✔️ Dine-in ✔️ Takeout ✔️ No delivery
Address:
337 High St, Chestertown, MD 21620
Phone: (443) 282-9797
Social Profile: 
Hours
| Monday
(Labor Day)
|
Closed |
| Tuesday | Closed |
| Wednesday | 3–9 PM |
| Thursday | 3–9 PM |
| Friday | 11:30 AM–9 PM |
| Saturday | 11:30 AM–9 PM |
| Sunday | 11 AM–2 PM |
Photo Gallery
Order and Reservations
Reservations: resy.com
Reviews
Patrick Shoemaker
An absolutely world class dining experience in Chestertown. We had the scallops and pork belly, and the lamb three ways dish. Both were delicious, and the greens we shared for a side, although they weren’t the eye candy that the mains were, tasted spectacular. Everyone we interacted with was friendly, professional, and laid back. Keep up the good work!
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patricia stabler
In town for the weekend and booked our dinner here . We arrived early and chose to sit at the bar tho they would have sat us , and enjoyed exquisite cocktails made by Sarah . Once seated the meal was top shelf from appetizer to dessert . My husband had the Spanish octopus that was so finely tuned in flavors and the preparation , amazing . I had the fried green tomato special that was amazing . My husband had the bison coulotte again cooked perfectly . I had the poussin , so tender ! The lemon brûlée was delicious , and the special peach dessert . Honestly from beginning to end a great experience . The chef came out to the table and we really enjoyed that ! Our server jennifer was great . Honestly one of the best fine dining experiences we have had . Worth the reservation !
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Rebecca Thomas
Jackson the bartender was our server tonight. Great recommendations and made us amazing drinks! Try the Sour Empress! The food was fresh and delicious and the staff was so warm & kind.
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Kevin Lutts
We arrived for happy hour and the owner had a 20 + min meeting with his staff 2 feet from our table, and the topic was ironically focused on how important customer service was. At the exact time while they completely ignored our table, did not serve our drinks and delayed ordering our meal. Staff was great but owner could actually practice what he was preaching., would have made for such a better dining experience if he at least apologized .
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Jen W
This hidden gem in Chestertown, MD is a must for anyone who enjoys outstanding food and service. We enjoyed the tuna crudo and octopus for an appetizer, both perfect in presentation and taste. The cod entree melted in your mouth. Kudos to Chef Thomas for that. I could not have asked for a better venison tenderloin, perfectly medium rare to rare with a simple, elegant sauce. The staff was professional, friendly, and very attentive. Jackson mixes a mean cocktail at the small bar. Leave DC, go to Watershed Alley.
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Heike Yates
We were in Rockhall for the Kinetic triathlon and wanted to check out some of the restaurants near by. This is not your typical pre race dinner but what an amazing surprise. The pictures don’t do the space justice. It is a mix of modern and elegant and just beautiful.
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Lauri Thomas
The service was impressive, they opened the door for us with a big smile. The food from the salad to the entrees was phenomenal. The cornbread was as good as mine! And the lemon brulee was the perfect finish to a lovely meal. Thanks.
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Julia Gonzalez
Our first time dining at Watershed Alley. Wow… everything was incredible. The decor, service and of course the decadent food!!! We drove a little over an hour and a half to dine there. We will certainly be returning!! Thank you Chip, Rodney, Audrey, and Jenn for a fabulous evening!!!
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Toni Lewis
Our second time here was just as wonderful as the first! Dining here is an experience in itself because you honestly forget that your in little ol’ Chestertown! The atmosphere is both classy and relaxing. The food is simply incredible, and the dessert…phenomenal! The talent in that kitchen is undeniable. I want to make sure I compliment the waitstaff as well. They were all so well mannered, prepared, and well trained. You can tell everyone there takes pride in their job and they truly want you to enjoy your time there. We are already looking forward to our next visit!
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Sharon A Ziolkowski
DEFINITE must!!!! The experience is like no other! From beautiful decor, which is all local art and craftsmanship, exceptional service to the scraping bowl for last bite cuisine. A LOT OF HEART AND SOUL went into this establishment and it shows! Don’t expect soup and salad to hit the table in 5 minutes because unlike every other restaurant around at Watershed Alley everything is made to order. Nothing is pre-preped or pre-heated. You really can’t go wrong with anything on the menu! Every item is prepared like a work of art all the way down to the specialty cocktails !! I say everyone deserves to treat themselves to this establishment. Whether you choose lunch or dinner, it is an experience unlike any other you will find on the Eastern Shore!!
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